Entropy Between Retreats

Many remote companies write about their retreats. They highlight the exotic destinations and fun activities. They talk about why they have retreats. I love reading those posts and comparing notes.

I've noticed something that happens at Tortuga that I haven't heard other remote companies mention: entropy.

entropy
noun
en·tro·py \ ˈen-trə-pē
a process of degradation or running down or a trend to disorder

Please forgive me the cliche of leading with a dictionary definition. I felt it was necessary.

Retreats don't just bring the team together in a literal way by sharing physical space. Our retreats work against entropy. Retreats get us realigned towards our mission.

I'm not sure how colocated companies experience this "trend to disorder." Every company must experience it to some degree. Before Tortuga, I'd only worked at Google, an enormous company. I'm sure that it was experiencing entropy. I was just too small of a cog to notice or care.

At Tortuga, I care.

Day-to-day and week-to-week, we have lots of small processes to keep us aligned.

I have 1:1s with everyone. We have a weekly email chain of what each person did the past week and what she will do next week. At the end of the month, we send team-level recap emails. We do biannual reviews.

No amount of process ever really feels like enough. Yet adding more isn't the solution.

Entropy happens. (Yes, there's a bumper sticker.)

Entropy is the default mode of an organization, particularly a growing one. The more you do, the more can and will break down. The more people you add, the harder it is to keep them working in perfect synchrony.

Retreats are the best way for us to counter this tendency. Outlining our strategy is more impactful in person. Being together in one room shows everyone how their work contributes to our collective progress as a team. Looking one's teammates in the eye reminds you that they are people, not just Slack avatars.

Then we leave the retreat and don't see each other in person for six months or more. The strategic alignment becomes less cohesive. Lines of communication degrade a bit. Those personal relationships weaken. Then we have another retreat and fight back against entropy. Between retreats, it gains ground. Then we push it back.

Retreat, entropy, retreat, repeat.